Keto-fluorothiopyranosyl nucleosides: a convenient synthesis of 2- and 4-keto-3-fluoro-5-thioxylopyranosyl thymine analogs

The synthesis of a single diastereomer of 3‐acetoxy‐2‐(trifluoromethyl)‐4‐hydroxy‐3,4‐dihydro‐2H‐thiopyran from the mixture of diastereomeric cycloadducts of p‐tolyl trifluorodithioacetate and 1‐acetoxybutadiene is described. Its acetylation and nucleophilic chlorination provides glycosylating agents with different leaving groups have been prepared. Their reactions with various O‐, S‐, N‐ and C‐nucleophiles have been studied. Depending on the conditions of the experiments, the reactions proceed as Ferrier (I) reactions affording 3‐acetoxy‐2‐(trifluoromethyl)‐6‐substituted‐3,6‐dihydro‐2H‐thiopyrans or as formal direct replacement of the leaving group in the position 4 giving 3‐acetoxy‐2‐(trifluoromethyl)‐4‐substituted‐3,4‐dihydro‐2H‐thiopyrans. The stereochemistry of the resulting products and all their precursors is discussed.

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Trifluoromethylated Thiopyranoid Glycals: Synthesis and Ferrier (I) Type Reactions

Siry

Shermolovich

Kinzhybalo

et al. 2018

Eur J Org Chem

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Stereocontrolled synthesis of 4′-C-cyano and 4′-C-cyano-4′-deoxy pyrimidine pyranonucleosides as potential chemotherapeutic agents

Kiritsis

Manta

Parmenopoulou

et al. 2012

Carbohydrate Research

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Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3′-C-trifluoromethyl and 3′-C-methyl pyranonucleosides

Kollatos

Manta

Dimopoulou

et al. 2015

Carbohydrate Research

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Keto-fluorothiopyranosyl nucleosides: a convenient synthesis of 2- and 4-keto-3-fluoro-5-thioxylopyranosyl thymine analogs

Cited by 5 publications

References 36 publications

Trifluoromethylated Thiopyranoid Glycals: Synthesis and Ferrier (I) Type Reactions

Trifluoromethylated Thiopyranoid Glycals: Synthesis and Ferrier (I) Type Reactions

Stereocontrolled synthesis of 4′-C-cyano and 4′-C-cyano-4′-deoxy pyrimidine pyranonucleosides as potential chemotherapeutic agents

Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3′-C-trifluoromethyl and 3′-C-methyl pyranonucleosides

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